David Foster Wallace

Why he’s daunting: David Foster Wallace wrote about lots of subjects with lots of strategies, all of them vehement. He could be vehemently searching, digressive, playful, pointed, self-conscious, or sad. He could be vehemently pedantic, moralistic, self-abnegating, or grand. His emphasis often changed among these modes, but the driving force was always there—to the extent that tangling with his work can be exhausting, for all the energy it extends to the reader and all the energy it expects back in kind. Chief among the conflicts presented to the Wallace newbie is the question of whether Wallace was better as a journalist or as a fiction writer. He did important work in both roles, but which, in the end, should prevail? Plus, how do we reconcile Wallace’s wisdom, clarity, and apparent glee in the face of all things complicated with the fact that he chose to end his own life?

Possible gateway: “A Supposedly Fun Thing I’ll Never Do Again”

Why: Wallace’s most important work lurks within his fiction, but, paradoxically, the best introduction to him comes by way of a travelogue essay he wrote with abundant misgivings on display. The title piece from A Supposedly Fun Thing I’ll Never Do Again, Wallace’s first collected book of non-fiction, is an essay written for Harper’s about a harried stay on a seven-night luxury cruise. In book form, it’s 96 pages long, and it’s outrageously funny and entertaining through all its longueurs. Most of Wallace’s trademark tricks and tics figure in: his keen self-consciousness, his electrifying way with words, his almost psychedelic fixation on detail. So does the abiding sense of purpose he brought to writing of every kind—a sense exemplified by a sentence tucked within a wry cataloguing of all he saw and did during a week alone among a mass of alien beings: “I have felt as bleak as I’ve felt since puberty, and have filled almost three Mead notebooks trying to figure out whether it was Them or Just Me.”

Next steps: The elephant in Wallace’s oeuvre, the one with blinking lights and flags sticking out of it, is Infinite Jest, the novel that made his name in 1996 and continues to impose by way of its size. It’s a big book, to be sure—1,079 pages, with nearly 100 given over to rhapsodic footnotes—but more monumental by far is its depth of feeling. At the core of it is a precocious tennis prodigy whose father happened to make an experimental film that threatens to zombify anyone who watches it. And then there’s the brilliant cast of drug addicts, a gang of Quebecois wheelchair assassins, a woman named Madame Psychosis, an NFL punter, and more. The jostle of it all is more than a little madcap, but Wallace’s greatest talent was for pure, stirring humanism—a kind of fiction whose empathy and understanding can make anything personal, and any person reading it wise to the distinction. Infinite Jest, it should also be noted, remains an absolute blast to read.

Wallace was also an ace with short fiction. The imagined Q&A transcripts laced through his great story collection Brief Interviews With Hideous Men are as revealing as they are aptly hideous, and the variously anguished and analytical stories in 2004’s Oblivion cover a startling range in terms of storytelling and approach. His later non-fiction took on increasingly serious and probing projects, from the ethical inquisition about eating lobster in his collection Consider The Lobster to a 2006 New York Times Magazine profile of tennis great Roger Federer that reads as nothing less than a consideration of all that is physical and mysterious about living in the world.

Where not to start: The question with Wallace is less where not to start and more where not to stop. No single one of his works does an especially good job of signaling what’s to be found in the rest of it, especially in terms of tenor and tone. The early metafiction games and conceits of younger, more showy Wallace—like those in his first story collection, 1989’s Girl With Curious Hair—would be pitched down, or at least redirected, over the years. And the fact remains that Wallace was always a good enough entertainer to adapt his greater literary project to whatever context he was working in. Two beloved sideline works that prove important in the end but should be held out for are the genuine math treatise Everything And More: A Compact History Of Infinity and This Is Water, a deeply moving commencement speech Wallace gave to Kenyon College in 2005. The latter was published as a tiny book after Wallace’s 2008 suicide; it looks more coy than it ideally should in its little impulse-buy form, but the speech itself proves huge for its humble, humane appeals to heart and reason.